tributyl((1E,3E,5E)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexa-1,3,5-trien-1-yl)stannane | 936483-04-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 英文名称: tributyl((1E,3E,5E)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexa-1,3,5-trien-1-yl)stannane
• 英文别名: tributyl-[(1E,3E,5E)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexa-1,3,5-trienyl]stannane
• CAS: 936483-04-4
• 化学式: C₂₄H₄₅BO₂Sn
• 分子量: 495.141
• InChiKey: RISFJUOSMBZDGX-NPXWGPKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.67
• 重原子数：
  28
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S,E)-3-iodo-N-(1-methoxypropan-2-yl)-2-methylacrylamide 、 tributyl((1E,3E,5E)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexa-1,3,5-trien-1-yl)stannane 在 tris(dibenzylideneacetone)dipalladium (0) 、 三苯胂 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以84%的产率得到(S,2E,4E,6E,8E)-N-(1-methoxypropan-2-yl)-2-methyl-9-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nona-2,4,6,8-tetraenamide
  参考文献：
  名称：

  Total Synthesis of 2‘-O-Methylmyxalamide D and (6E)-2‘-O-Methylmyxalamide D

  摘要：

  Hetero-bis-metalated 1,3,5-hexatrienes are employed in the linchpin coupling of synthetic fragments for the convergent construction of the central pentaene of the antifungal agent 2'-O-methylmyxalamide D and its (6E) isomer. Sequential Stille and Suzuki-Miyaura couplings interpolate the boron/tin triene into the pentaene chain. The total synthesis of O-methylmyxalamide D and its (6E) isomer was accomplished efficiently.

  DOI：

  10.1021/ja070265e
• 作为产物：
  描述：

  (2E,4E)-5-(tributylstannyl)penta-2,4-dienal 、 频哪醇(二氯甲基)硼酸酯 在 chromium dichloride 、 lithium iodide 作用下， 以 not given 为溶剂， 以70%的产率得到tributyl((1E,3E,5E)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexa-1,3,5-trien-1-yl)stannane
  参考文献：
  名称：

  Total Synthesis of 2‘-O-Methylmyxalamide D and (6E)-2‘-O-Methylmyxalamide D

  摘要：

  Hetero-bis-metalated 1,3,5-hexatrienes are employed in the linchpin coupling of synthetic fragments for the convergent construction of the central pentaene of the antifungal agent 2'-O-methylmyxalamide D and its (6E) isomer. Sequential Stille and Suzuki-Miyaura couplings interpolate the boron/tin triene into the pentaene chain. The total synthesis of O-methylmyxalamide D and its (6E) isomer was accomplished efficiently.

  DOI：

  10.1021/ja070265e

文献信息

• Efficient synthesis of diverse hetero-bis-metallated alkenes as modular reagents towards highly conjugated and isolated olefinic systems
  作者：Mario Altendorfer、Dirk Menche

  DOI：10.1039/c2cc34052f

  日期：——

  An efficient synthesis of diverse hetero-bis-metallated alkenes with conjugated and isolated olefin subunits is reported. Relying on those useful tin/boron reagents a convergent, palladium-catalyzed fragment coupling strategy has been developed as an elegant methodology to construct highly conjugated polyenes and stabilized olefinic analogues thereof. The utility of these reagents was further demonstrated in a concise and modular construction of extended polyene side chains of the potent polyketide antibiotic etnangien.

  报道了一种高效合成多样性杂双金属化烯烃的方法，这些烯烃具有共轭和孤立的烯烃亚单位。依靠这些有用的锡/硼试剂，开发了一种收敛的、钯催化的片段偶联策略，作为构建高度共轭的聚烯烃及其稳定的烯烃类似物的优雅方法。这些试剂的实用性进一步通过简明且模块化的构建强效多酮类抗生素etnangien的延伸聚烯烃侧链得到了验证。